Renowned American yacht designer Nathaneal Herreshoff designed this radical sailboat. All of the racing yachts of “Dilemma”’s day had heavy keels that ran the full length of the boat. Herreshoff gave “Dilemma” a “fin keel,” centering all the weight in a bulb at the base. He also moved the rudder back from the trailing edge of the keel to make the boat more responsive to steering.

“Dilemma” won every race she entered, and yacht designers quickly began emulating Herreshoff’s design. “Dilemma” inspired the design not only of the 1967 America’s Cup defender, “Intrepid”, but of all the current America’s Cup yachts as well.